Interviewing for Your Next Product Leadership Role
Trusting Your Gut in this Turbulent Market
I had an entirely different subject planned for this month’s newsletter. I had a first draft written but I put it on hold after having a conversation with a peer this week who is starting to look for a new role. I know so many product management leaders are looking for their next gig right now. Unfortunately, so many is an understatement. I recently saw this post on LinkedIn from one of the most well-connected people in tech I know. In her network one in two seasoned product management leaders are looking for work and many of those individuals have been looking for more than six months. 👀 This is really why I felt compelled to change plans and write on the topic of interviewing in this market.
I went through my own existential journey earlier this year figuring out what I wanted next. If you’re a new reader and curious, this is the post where I share my journey figuring it out. Ultimately I decided to a full-time role was the right fit for my skills and my needs. It’s that experience I drew from when chatting with my peer last week. Our discussion went in a few different directions but the main thing takeaway I had from that conversation was once you know what you want next, the hardest part in this market is holding fast to your needs, making a choice with eyes wide open, and trusting your gut on whether it is a fit once you make it through the gruelling interview cycle.
Figuring Out & Finding the Next Right Product Leadership Gig
There’s a plethora of advice on how to help you land your next gig. In my experience, the first place I’d send you is the Never Search Alone book & the online community started by Phyl Terry. Phyl was recently featured on Lenny’s Podcast. It’s well worth the listen if you’re currently in transition.
I don’t want to re-hash Terry’s content here but I can share what I found most valuable from my Never Search Alone experience: applying discovery techniques to my job search.
Exploration & Defining your Unique Value Proposition
In Never Search Alone there is a discovery phase to help you figure out what you want next and what you are best positioned to offer your next company. When most people start job searching they dust off the old resume and start sending it out. Terry advises against this instinct, instead he suggests you take the time to pause and reflect before executing on the job search. Sounds familiar right?
This phase is tortuously long, especially if you were laid off. However, any product leader knows the upfront effort in discovery is worth it. The two core concepts of this phase are distilled into one artifact: a 1-Pager that highlights your personal unique value proposition, in Terry’s terms: “candidate-market fit.” It’s a product brief for you, drafted after many conversations with old colleagues and peers to help you refine what you love and hate about work and what you’re awesome and not so awesome at.
I’ve screenshot one part of my own 1-Pager as an example. It took weeks and weeks to refine mine into this version. My advice is to give the exercises the space and time deserved to clarify your vision for yourself. It makes all the decision making down the road so much easier.
Highly recommend you buy the book and follow the advice.
Prepare & Trust Your Instincts
Now onto the tough part you are all familiar with. Chatting with my peer last week one of the things they found so difficult looking for a new role was assessing the company appropriately. This concern resonated deeply with me.
While interviewing with my current company I had done extensive preparation and took the time to reflect throughout the interview process at every stage to make sure every step forward was one worth taking. During our conversation I pulled up a Google doc I used to guide my thinking during the interview cycle and shared some of my tips and tricks for assessing the fit. After our call I decided to rip out the specifics in that doc and turn it into a template to share with them. I decided to share it with all of you as well, you’ll find the link to the template at the bottom of the page. 👇
This process proved invaluable to me. It helped me showcase my skills effectively and determine if a company was the right fit for me.
BEFORE YOU INTERVIEW
Preparing for a product leadership interview requires a strategic approach. Here's how I prepare for product leadership interviews:
The 101 & Stories to Tell
I write out the following six things before starting any interview process.
My Past/Present/Future:
Past: Elevator Pitch for myself; it’s why I’m amazing
Present: Where I’m at; why I’m looking
Future: What I want next; why this role aligns with what I want
Why this Company: The specifics of the company (product, maturity, challenge) & why it’s a fit for me
Dragon Slaying Story: A highlight in my product career that is a compelling story. Specifically I would talk about the new product I took from MVP to PMF going from $0 to $20M in a few years.
Biggest Failure & What You Learned from it: I prepare myself for humility; I lean on honesty here because it’s critical at a leadership level.
Strengths: What value I bring.
Weaknesses/Areas for Growth: My liabilities. Often they are the shadow (anti-thesis) to my super powers.
While I lean into honesty in the above and most of these bullet points remain the same from company to company I also take the time to prepare compelling stories from my part experience that are directly related to the job description. Inevitably, in product leadership roles, there’s three main themes in the job description:
Leadership & Management of a product management team & leadership capabilities
Product Strategy is the ability to align product roadmap with business growth
Collaboration and Communication up, down, and across all functions in the company
I use ChatGPT to analyze the job description to identify key themes — if the above three are off the mark — and required skills related to role. Once I have that breakdown I come up with a story for every skill using the STAR framework (Situation, Task, Action, Result).
At the end of this exercise I’m armed for whatever questions come my way during the initial stages of the interview process: typically for the talent screen and early behavioural focused interviews.
DURING THE INTERVIEWS
Vibe Check after Every Interview Stage
I earmark 15 minutes after every interview to reflect on how it went. Don’t skip this — it's your chance to assess the company while the memories are fresh. Time leaves room for bias to creep in. Personally I find the more time I take the more optimistic I get about the opportunity and I start to ignore the red flags.
Immediately after every interview I ask myself a series of questions. See the image below for examples.
These can be adjusted based on what your priorities are, but generally these are a good place to start for culture fit and expertise. The killer question that has helped me every time is:
“Were you uncomfortable with anything you cannot put your finger on?”
After asking myself these questions I compile a list of positives and red flags. These directly co-relate to my 1-pager: what I must/must not have in my next role and whether the role needs my particular cocktails of strengths. This gives me a clear picture of whether I should pursue this position or gracefully back out.
I make a concerted effort to trust my instincts immediately after the interview. This prevents time and my own mind from working against me, potentially obscuring something that didn't feel right. In this challenging job market, it's tempting to pursue any role you're considered for. I know, we have bills to pay and mouths to feed. However, if the red flags are accumulating, you owe it to yourself to inquire about them or thoroughly examine the trade-offs you'd face in dealing with them.
Job Mission & OKRs
Another thing I prepare during the job interview process comes from Never Search Alone, and that’s defining the “job mission” and drafting OKRs for the role. At a certain point in the interview process you’ll have enough information to write this out. It may not be perfectly accurate — I just went back to mine from my new job and one OKR was really off-base but the other two were relevant and reminded me what I need to be doing in my first few months to stay on track.
If it sounds like a lot of work, it’s because it is. Apparently Terry says many people who use Never Search Alone don’t do this step at all out of fatigue or embarrassment at being so brazen to set your own goals before you start. But I’ll tell you it was critical in closing the role at my current company. It demonstrated to my VP of Product and the executive team that I was thoughtful about challenge ahead of me. And that I wanted to take that challenge on headfirst because I was aware of the challenge in addition to the perks that came with the role. If you get to this point in interviewing and you know the role is the right fit, in my humble opinion, this exercise help you close the deal.
OFFER IN HAND
Okay, so you have the offer in hand. Now what? You’re feeling the pressure to take the job. If you don’t, you’ll be another one in two product leaders unemployed for six plus months. I hear you, but maybe there’s a few red flags you need to consider from the interview process first. I recently was joking with some co-workers about the importance of “spidey sense” in your role as a leader. We all laughed how we use the phrase “spidey sense” but all thoughtfully nodded when we agreed it has never led us astray. When the offer is in your hand, it’s time to channel your inner Spider-Man and listen to that tingle.
There’s two things I do once I have a job offer in hand is to lean into what spidey sense is telling me:
Go back to my 1-Pager.
It tells the story of what I want next, so I need to really assess if this role lines up with enough of those bullet points. If it doesn’t I have to make a conscious choice to proceed knowing that it doesn’t. If you go back to your 1-Pager and you’re 80-90% covered by this role; you’ll know whether you’re comfortable with that fit. If the delta is wider than that you’ve got harder questions to ask yourself. It’s hard to do this only by yourself.Do my due diligence.
I vet the role with the right people: current employees with enough insight and relevant to my role to weigh in, my own peer group of trusted advisors, and the hiring manager for this role. I need to leverage every source of information available to me to make the best decision for me.
The standard advice is to vet the company with current employees. I’ve done this in the past and it’s bit me in the ass — people aren’t honest. I still encourage you to have those conversations, but do that with open eyes. Ask yourself: Is the person you’re talking to actually in the know about your role and department? or Is the person I’m talking to at a similar seniority level? Do they understand the context I’m walking into? Sometimes, other back channels can provide a better way to assess fit than current employees. For example, someone in your network who has previously worked with one of the founders or your potential manager. While this person might have some bias, they could also offer practical advice from a more distanced perspective. Take all outside opinions with a grain of salt.
The second step is to collect your trusted crew together — the people who’ve been walking alongside you in this journey of finding the next role. Talk to the people who read your 1-pager and your “candidate-market fit” statement; they will help you make the call when something is or isn’t right. I recently was on a video call with a peer of mine who wanted help to prep for an interview. Five minutes into the conversation we realized she did not want this role and it wasn’t worth her time prepping for an interview. And she was looking because of a layoff. Only you know your situation and whether you can make this choice; but a trusted friend can help you make the call. It’s not selfish, it’s strategic - you are being effective with your most valuable resource: your time and energy.
The final step in my due diligence process when vetting an offer is to discuss my hesitations with the hiring manager before accepting. Even for my current role, which was an excellent fit, I had a few concerns that needed addressing. I made sure to have this conversation with my future manager. My concerns were met with straightforward acknowledgment and satisfactory answers, so I proceeded. However, if you sense any defensiveness in response to your questions when having this discussion, trust your instincts.
On the other hand, if you feel strongly about the direction you want to take, there's another approach worth considering. A peer of mine recently shared an interesting strategy: when faced with a decision she's leaning towards, she seeks out someone who will strongly oppose it. This creates an opportunity to defend her decision-making process. If she struggles to defend her stance during the conversation, she realizes her convictions were not as strong as she thought and needs to reassess. However, if she can confidently defend her perspective, she knows she's made the right choice. I found this advice extremely compelling! While it requires a high degree of self-awareness, it's a technique I'm eager to try the next time I'm confronted with a difficult decision.
Listen to your "spidey sense" in these situations; you need a salary but at what cost? Only you know the answer to that trade off.
Final Thoughts
Let’s be real this is a lot of fucking work to just land a job. On the flip side, we make good money so there’s a reason it’s a lot of fucking work. But here's how I see it: my career and sanity on the line if I screw up; so I better put in the effort. For me, my career and my life are intertwined. Happy job, happy life. The effort was, and will continue to be, worthwhile for me.
In this job market, there will be a few paths for product management leaders to consider: leave the industry, leave the field, start consulting, or you find the next right role. My hot take: I think product management is contracting not expanding. But I don’t think it’s going to be a total extinction. The best of the best will remain in the craft working for companies who need fewer product people to bring their vision to life. Choose accordingly base on your preference.
If you’re in transition, pick the path that works for you. I chose to stay the traditional route. If you’re choosing that path too, I hope the newsletter today will help you make the best decisions as you take that path forward. Trust your gut.
Resource
This is the template I use for interviewing. Take it, adapt it, share it.